Place the pitted dates in a mixing bowl and cover with boiling water, and let sit for 5 minutes.
While the dates are soaking, place your skillet over medium heat and add your coconut shreds. Toss and toast for about 5 minutes, until the coconut becomes very fragrant and starts to turn a golden brown.
Drain the dates and add to a food processor along with the toasted coconut, almond flour, and vanilla. Pulse until a paste is formed.
Place your date and coconut mixture into the fridge for 20 minutes to harden up. This makes rolling the cookies much easier.
After your date mixture had chilled, take about 1 to 2 tbsp of the mixture and roll into a ball, then flatten into a cookie shape and place on a lined baking sheet. Repeat until all the date mixture is gone.
Once all the cookies are rolled out, place them in the freezer for 10 minutes. This will help solidify them before dipping them in the chocolate.
Add the dark chocolate and coconut oil to a microwave-safe dish. Heat in 20-second increments until the chocolate and coconut oil are a smooth liquid. Gently dip one side of your date cookies into the chocolate and set them back on the lined baking sheet. Repeat with all of the date cookies. If you would like, sprinkle with flaky sea salt when the chocolate is still wet.
Once the chocolate is set, the cookies are ready to serve!
Storage Instructions: Store your cookies in an airtight container in the refrigerator for up to 10 days to keep the chocolate snappy and the coconut base chewy. They also freeze beautifully for up to 3 months—just let them thaw for 5 minutes before serving.